Manganese‐Catalyzed <i>anti</i>‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides

Zhang, Linli; Wang, Zheng; Han, Zhaobin; Ding, Kuiling

doi:10.1002/ange.202006383

Cited by 25 publications

(1 citation statement)

References 62 publications

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“…In view of current interest in the development of earth-abundant metal catalysts in asymmetric hydrogenation 31 – 41 , which are inexpensive and environmentally friendly, the use of nickel has drawn increasing attention 24 , 31 – 41 . Although Ni-catalyzed asymmetric reduction has seen rapid development, the asymmetric hydrogenation of imines is still in its infancy 24 , 42 – 44 .…”

Section: Introductionmentioning

confidence: 99%

Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines

Liú

Chen

et al. 2020

Nat Commun

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Chiral α-aryl glycines play a key role in the preparation of some bioactive products, however, their catalytic asymmetric synthesis is far from being satisfactory. Herein, we report an efficient nickel-catalyzed asymmetric hydrogenation of N-aryl imino esters, affording chiral α-aryl glycines in high yields and enantioselectivities (up to 98% ee). The hydrogenation can be conducted on a gram scale with a substrate/catalyst ratio of up to 2000. The obtained chiral N-p-methoxyphenyl α-aryl glycine derivatives are not only directly useful chiral secondary amino acid esters but can also be easily deprotected by treatment with cerium ammonium nitrate for further transformations to several widely used molecules including drug intermediates and chiral ligands. Formation of a chiral Ni-H species in hydrogenation is detected by 1H NMR. Computational results indicate that the stereo selection is determined during the approach of the substrate to the catalyst.

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Section: Introductionmentioning

confidence: 99%

Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines

Liú

Chen

et al. 2020

Nat Commun

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Iridium‐Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’‐Keto‐β‐Amino Esters via Dynamic Kinetic Resolution

et al. 2021

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An iridium/f‐diaphos catalytic system for the enantioselective hydrogenation of α‐substituted β‐ketoesters via dynamic kinetic resolution is reported. The desired anti β’‐hydroxy‐β‐amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading (TON up to 9100).

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Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

Zhou

Zhang

et al. 2023

Adv Synth Catal

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The RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, (S)‐Orphenadrine and (S)‐Neobenodine. Deuterium labeling and control experiments revealed that the RuPHOX‐Ru‐catalyzed asymmetric hydrogenation is fully subject to hydrogenation with H2 as the sole hydrogen source.

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Manganese‐Catalyzed anti‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides

Cited by 25 publications

References 62 publications

Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines

Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines

Iridium‐Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic β’‐Keto‐β‐Amino Esters via Dynamic Kinetic Resolution

Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

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